2-(furan-2-yl(hydroxy)methyl)cyclohexan-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(furan-2-yl(hydroxy)methyl)cyclohexan-1-one
• 英文别名: 2-[2-Furyl(hydroxyl)methyl]-cyclohexanone；2-[furan-2-yl(hydroxy)methyl]cyclohexan-1-one
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: KCWNWTJIORDVNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-<(2-furyl)trimethylsiloxymethyl>cyclohexanone 生成 2-(furan-2-yl(hydroxy)methyl)cyclohexan-1-one
  参考文献：
  名称：

  KAWAI, MOTOMITSU;ONAKA, MAKOTO;IZUMI, YUSUKE, BULL. CHEM. SOC. JAP., 61,(1987) N 4, 1237-1245

  摘要：

  DOI：

文献信息

• Prolinamides of Aminouracils, Organocatalyst Modifiable by Complementary Modules
  作者：Karen M. Ruíz-Pérez、Beatriz Quiroz-García、Marcos Hernández-Rodríguez

  DOI：10.1002/ejoc.201800886

  日期：2018.11.8

  Prolinamide organocatalysts with aminouracils have the features of enhanced NH acidity, an additional hydrogen‐bond donor and the self‐assembly with complementary modules by Watson–Crick pairing. Each module affects the selectivity of the reaction and particularly 2,6‐diaminopyridine is beneficial to the selectivity in the reaction.

  带有氨基尿嘧啶的脯氨酰胺有机催化剂具有增强的NH酸度，额外的氢键供体以及通过沃森-克里克配对与互补模块自组装的特点。每个模块都会影响反应的选择性，特别是2,6-二氨基吡啶对反应的选择性有益。
• Design and preparation of a novel prolinamide-based organocatalyst for the solvent-free asymmetric aldol reaction
  作者：Rafaela de S. Martins、Mathias P. Pereira、Pedro P. de Castro、Fernanda I. Bombonato

  DOI：10.1016/j.tet.2019.130855

  日期：2020.1

  proline-derived catalyst, providing access to the desired adducts in up to 95% yield, 1:19 syn/anti and 98% e.e. Moreover, even sterically bulky aldehydes and substituted cyclohexanones were well tolerated. DFT calculations and control experiments indicated that several hydrogen bonding interactions between the aldehyde and the enamine intermediate are responsible for the stereoselective chiral induction process

  描述了四种新型有机催化剂的制备，这些催化剂是用于无溶剂不对称醛醇缩合反应的高度非对映体和对映体选择性催化剂。这些有机催化剂使用简单的市售起始原料分八步合成。脯氨酸衍生的催化剂获得了最佳结果，以高达95％的收率，1：19合成/反合成获得所需的加合物和98％ee此外，即使空间上较大的醛和取代的环己酮也具有良好的耐受性。DFT计算和对照实验表明，醛与烯胺中间体之间的几种氢键相互作用是立体选择性手性诱导过程的原因，而三氟乙酸抗衡阴离子对于实现更高的立体选择性至关重要。
• Novel sulfonylpolystyrene-supported prolinamides as catalysts for enantioselective aldol reaction in water
  作者：Rafael Pedrosa、José M. Andrés、Ana Gamarra、Rubén Manzano、César Pérez-López

  DOI：10.1016/j.tet.2013.10.093

  日期：2013.12

  Five novel prolinamides derived from 1,n-diamines supported on commercially available sulfonylpolystyrene have been synthesized and successfully applied in diastereo- and enantioselective aldol reaction in water or, in one case, neat conditions. Excellent dr and er were obtained by reaction of different cyclohexanone derivatives with aromatic and heteroaromatic aldehydes in the presence of the catalysts

  已经合成了五种衍生自负载在市售磺酰基聚苯乙烯上的1，正二胺的五种新型脯氨酰胺，并将其成功地用于水中或在纯净条件下的非对映体和对映体选择性羟醛反应中。在催化剂和以AcOH为助催化剂的情况下，通过不同环己酮衍生物与芳族和杂芳族醛的反应获得了优异的dr和er。负载的有机催化剂在低负荷（5摩尔％）下工作，表现出与均相脯氨酰胺相似的性能，并且在活化后可以重复使用，而不会损失活性。
• Trimethylsilyl trifluoromethanesulfonate-catalyzed aldol reaction of various aldehydes with silyl enol ethers.
  作者：Chisato MUKAI、Satoshi HASHIZUME、Kazuyoshi NAGAMI、Miyoji HANAOKA

  DOI：10.1248/cpb.38.1509

  日期：——

  The aldol reaction of trimethylsilyl enol ethers (1-3) with various aldehydes in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate was investigated. With benzaldehyde (4) the β-hydroxycarbonyl compounds were obtained in good yields. The effect of a substituent on the benzene ring was also examined. Aliphatic aldehydes (11, 13, and 14) were found not to be suitable substrates for this catalytic aldol reaction. On treatment with tert-butyldimethylsilyl enol ethers (30 and 31) under the same conditions, benzaldehydes (4, 5, 7, 8) yielded the corresponding aldol products with good threo-selectivity.

  在三氟甲磺酸三甲基硅酯的催化量存在下，研究了三甲基硅基烯醇醚（1-3）与各种醛的羟醛反应。与苯甲醛（4）反应时，可以得到产率良好的β-羟基羰基化合物。同时还考察了取代基对苯环的影响。发现脂肪醛（11、13和14）不适宜作为这一催化羟醛反应的底物。在相同条件下与叔丁基二甲基硅基烯醇醚（30和31）反应时，苯甲醛（4、5、7、8）能够产生具有良好苏式选择性的相应羟醛产物。
• (1R,2R)-Bis[(S)-prolinamido]cyclohexane Modified with Ionic Groups: The First C2-Symmetric Immobilized Organocatalyst for Asymmetric Aldol Reactions in Aqueous Media
  作者：Sergei V. Kochetkov、Alexandr S. Kucherenko、Sergei G. Zlotin

  DOI：10.1002/ejoc.201100707

  日期：2011.10

  The first C2-symmetric immobilized organocatalyst for asymmetric aldol reactions containing the (1R,2R)-bis[(S)-prolinamido]cyclohexane unit tagged with two imidazolium+/PF6– ion pairs has been synthesized. In its presence, (hetero)aromatic aldehydes reacted with linear or cyclic ketones in aqueous media to yield chiral aldols with high diastereo- and enantioselectivities and the catalyst could be

  已经合成了第一个用于不对称醛醇反应的 C2 对称固定化有机催化剂，该催化剂包含 (1R,2R)-双 [(S)-脯氨酰胺] 环己烷单元，并用两个咪唑鎓+/PF6- 离子对标记。在它的存在下，（杂）芳族醛与线性或环状酮在水性介质中反应以产生具有高非对映选择性和对映选择性的手性醛醇，并且催化剂可以回收和重复使用至少 10 次，而反应速率或选择性没有任何降低。